US6358633B1 - Organic electroluminescence element - Google Patents

Organic electroluminescence element Download PDF

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US6358633B1
US6358633B1 US09/308,818 US30881899A US6358633B1 US 6358633 B1 US6358633 B1 US 6358633B1 US 30881899 A US30881899 A US 30881899A US 6358633 B1 US6358633 B1 US 6358633B1
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organic electroluminescent
dopant
host material
electroluminescent device
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Takeshi Sano
Yoshitaka Nishio
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Sanyo Electric Co Ltd
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    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00Organic light-emitting devices
    • H10K50/10OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • CCHEMISTRY; METALLURGY
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    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • HELECTRICITY
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    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60Organic compounds having low molecular weight
    • H10K85/615Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60Organic compounds having low molecular weight
    • H10K85/615Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/624Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
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    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60Organic compounds having low molecular weight
    • H10K85/615Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/626Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
    • HELECTRICITY
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    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2102/00Constructional details relating to the organic devices covered by this subclass
    • H10K2102/10Transparent electrodes, e.g. using graphene
    • H10K2102/101Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO]
    • H10K2102/103Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO] comprising indium oxides, e.g. ITO
    • HELECTRICITY
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    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/10Organic polymers or oligomers
    • H10K85/141Organic polymers or oligomers comprising aliphatic or olefinic chains, e.g. poly N-vinylcarbazol, PVC or PTFE
    • H10K85/146Organic polymers or oligomers comprising aliphatic or olefinic chains, e.g. poly N-vinylcarbazol, PVC or PTFE poly N-vinylcarbazol; Derivatives thereof
    • HELECTRICITY
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    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30Coordination compounds
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    • H10K85/00Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30Coordination compounds
    • H10K85/321Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
    • H10K85/324Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3
    • HELECTRICITY
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    • H10K85/00Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30Coordination compounds
    • H10K85/381Metal complexes comprising a group IIB metal element, e.g. comprising cadmium, mercury or zinc
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    • H10K85/00Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60Organic compounds having low molecular weight
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60Organic compounds having low molecular weight
    • H10K85/649Aromatic compounds comprising a hetero atom
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S428/00Stock material or miscellaneous articles
    • Y10S428/917Electroluminescent
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10TTECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00Stock material or miscellaneous articles
    • Y10T428/24Structurally defined web or sheet [e.g., overall dimension, etc.]
    • Y10T428/24942Structurally defined web or sheet [e.g., overall dimension, etc.] including components having same physical characteristic in differing degree

Definitions

  • the present invention relates to an organic electroluminescent device constructed by forming at least an emitting layer using an organic material between a hole injection electrode and an electron injection electrode, and is characterized in that stable luminance can be obtained for a long time, and high luminance can be obtained at a low voltage particularly in an organic electroluminescent device having an emitting layer constructed by doping a dopant into a host material.
  • the electroluminescent device is roughly divided into an inorganic electroluminescent device and an organic electroluminescent device depending on a used material.
  • the inorganic electroluminescent device is so adapted that a high electric field is generally applied on a luminance portion, and electrons are accelerated within the high electric field to collide with a luminescence center, whereby the luminescence center is excited to emit light.
  • the organic electroluminescent device is so adapted that electrons and holes are respectively injected into a luminescent portion from an electron injection electrode and a hole injection electrode, the electrons and the holes thus injected are recombined with each other in a luminescence center to bring an organic molecule into its excited state, and the organic molecule emits fluorescence when it is returned from the excited state to its ground state.
  • the inorganic electroluminescent device In the case of the inorganic electroluminescent device, a high voltage of 100 to 200 volts is required as its driving voltage because the high electric field is applied as described above. On the other hand, the organic electroluminescent derive can be driven at a low voltage of approximately 5 to 20 volts.
  • a luminescent device emitting light in a suitable color can be obtained by selecting a fluorescent material that is a luminescent material. It is expected that the organic electroluminescent device can be also utilized as a multi-color or full-color display device, for example. Further, it is considered that the organic electroluminescent device is utilized as a back light of a liquid crystal display device or the like because it can emit light at a low voltage.
  • an emitting layer and a carrier transport layer which is constituted by a hole transport layer for transporting holes to the emitting layer and an electron transport layer for transporting electrons thereto are generally provided between a hole injection electrode and an electron injection electrode.
  • a three-layer structure referred to as a DH structure obtained by laminating a hole transport layer, an emitting layer and an electron transport layer between a hole injection electrode and an electron injection electrode a two-layer structure referred to as an SH-A structure obtained by laminating a hole transport layer and an emitting layer abundant in electron transport properties between a hole injection electrode and an electron injection electrode
  • a two-layer structure referred to as an SH-B structure obtained by laminating an emitting layer abundant in hole transporting properties and an electron transport layer between a hole injection electrode and an electron injection electrode.
  • organic electroluminescent device In a conventional organic electroluminescent device, however, it is generally difficult to obtain as an organic material used for its emitting layer high-purity one by sublimation and purification, for example, and the stability of the organic material to heat or the like is not sufficient.
  • the organic electroluminescent device emits light for a long time, therefore, some problems occur.
  • the organic material used for the emitting layer is crystallized to form pinholes due to heat or the like at the time of the light emission, so that uniform and sufficient luminance cannot be obtained for a long time.
  • An object of the present invention is to solve the above-mentioned problems in an organic electroluminescent device constructed by forming at least an emitting layer using an organic material between a hole injection electrode and an electron injection electrode.
  • an object of the present invention is to make it possible to obtain stable luminance for a long time by preventing pinholes from being formed by crystallization of an organic material used for an emitting layer due to heat or the like at the time of emitting light as in the conventional example.
  • Another object of the present invention is to make it possible to obtain, in an organic electroluminescent device having an emitting layer obtained by doping a dopant into a host material, high luminance by sufficient light emission of a dopant doped into the host material in the emitting layer.
  • the present invention is so adapted, in an organic electroluminescent device constructed by providing at least an emitting layer using an organic material between a hole injection electrode and an electron injection electrode, that a dopant selected from coronene, rubicene, pyrene, benzpyrene, chrysene, ovalene, fluorocyclene, picene, triphenylene, aceanthrene, fluoranthene, acenaphthene, acenaphthylene, benzanthracene, naphthafluorene, naphthafluorenone, naphthapyrene, anthraquinone, rubrene peroxide, pentacene quinone, perylene quinone, naphthacene quinone, benzofluorenone, benzofluorene, anthrafluorene, benzperylene, benzpentacene, bispyrenyl propane, tetramethyl nap
  • the above-mentioned dopant is low in molecular polarity, is easily sublimated, and has high heat resistance. Therefore, a high-purity dopant is easily obtained by sublimation and purification. When the high-purity dopant which is thus obtained by the sublimation and purification is doped into the emitting layer, uniform and higher luminance is obtained for a long time.
  • FIG. 1 is a schematic explanatory view of an organic electroluminescent device having an SH-A structure obtained by laminating a hole transport layer and an emitting layer between a hole injection electrode and an electron injection electrode;
  • FIG. 2 is a schematic explanatory view of an organic electroluminescent device having an SH-B structure obtained by laminating an emitting layer and an electron transport layer between a hole injection electrode and an electron injection electrode;
  • FIG. 3 is a schematic explanatory view of an organic electroluminescent device having a DH structure obtained by laminating a hole transport layer, an emitting layer and an electron transport layer between a hole injection electrode and an electron injection electrode;
  • FIG. 4 is a schematic explanatory view showing structures of organic electroluminescent devices in examples 1 to 31 and comparative examples 1 to 8;
  • FIG. 5 is a schematic explanatory view showing structures of organic electroluminescent devices in examples 32 to 35 and comparative examples 9 and 10.
  • the organic electroluminescent device may have any one of known structures such as an SH-A structure obtained by laminating a hole transport layer 3 and an emitting layer 4 between a hole injection electrode 2 and an electron injection electrode 6 which are formed on a transparent substrate 1 such as a glass substrate, as shown in FIG. 1, an SH-B structure obtained by laminating an emitting layer 4 and an electron transport layer 5 between the hole injection electrode 2 and the electron injection electrode 6 , as shown in FIG. 2, and a DH structure obtained by laminating a hole transport layer 3 , an emitting layer 4 and an electron transport layer 5 between the hole injection electrode 2 and the electron injection electrode 6 , as shown in FIG. 3 .
  • a dopant having a condensed ring obtained by condensing three or more rings is doped into a host material in the emitting layer 4 , and the difference between the highest occupied molecular orbital (hereinafter referred to as HOMO) in the host material and the highest occupied molecular orbital (HOMO) in the dopant is set in a range from ⁇ 0.3 eV to +0.3 eV.
  • HOMO highest occupied molecular orbital
  • a material having a large work function for example, gold or an indium-tin oxide (hereinafter referred to as ITO) is used for the hole injection electrode 2
  • an electrode material having a small work function for example, a material including a magnesium alloy, an alkali metal or an alkali earth metal is used for the electron injection electrode 6 .
  • At least one of the electrodes must be made transparent in order to take out light emitted in the emitting layer 4 .
  • ITO which is transparent and has a large work function is used for the hole injection electrode 2 .
  • a transparent hole injection electrode 2 having a thickness of 2000 ⁇ was formed using the above-mentioned ITO on a glass substrate 1 , and a first hole transport layer 3 a having a thickness of 600 ⁇ using a triphenylamine derivative (hereinafter referred to as MTDATA) indicated by the following chemical formula 1, a second hole transport layer 3 b having a thickness of 200 ⁇ using NPD indicated by the following chemical formula 2, an emitting layer 4 having a thickness of 500 ⁇ obtained by doping 2% by weight of coronene having a melting point of 438° C.
  • MTDATA triphenylamine derivative
  • coronene indicated by the foregoing chemical formula 4 to be contained as a dopant in the emitting layer 4 was one having purity of 99% obtained by sublimating and purifying commercially available coronene (produced by Tokyo Kasei Kogyo Co., Ltd.) for 12 hours using a vacumm heating type sublimating and purifying apparatus. The yield of the coronene which was thus sublimated and purified was 60%.
  • the glass substrate 1 having the hole injection electrode 2 composed of ITO formed on its surface was cleaned by a neutral detergent, was ultrasonically cleaned in extrapure water, acetone, and ethanol, respectively, for 20 minutes, 20 minutes, and 20 minutes, was further put in boiling ethanol for about one minute and taken out, and was then immediately dried by ventilation, after which the surface of the glass substrate 1 was cleaned for ten minutes using a UV-ozone cleaner.
  • the above-mentioned MTDATA was vacuum evaporated over the hole injection electrode 2 formed on the glass substrate 1 , to form the first hole transport layer 3 a, and the above-mentioned NPD was then vacuum evaporated, to form the second hole transport layer 3 b.
  • the above-mentioned Zn(OXZ) 2 and coronene were co-evaporated over the second hole transport layer 3 b, to form the emitting layer 4 , and a magnesium-indium alloy was further vacuum evaporated over the emitting layer 4 , to form the electron injection electrode 6 .
  • the vacuum evaporation was performed at a degree of vacuum of 1 ⁇ 10 ⁇ 6 Torr.
  • An organic electroluminescent device in a comparative example 1 was obtained in the same manner as that in the above-mentioned example 1 except that only the emitting layer 4 in the organic electroluminescent device in the example 1 was changed, and only the above-mentioned Zn(OXZ) 2 which is the host material was used, to form an emitting layer 4 .
  • An organic electroluminescent device in a comparative example 2 was also obtained in the same manner as that in the above-mentioned example 1 except that only the emitting layer 4 in the organic electroluminescent device in the example 1 was changed, and 2% by weight of coumarin 4 having a melting point of 70° C. indicated by the following chemical formula 5 was doped into the above-mentioned Zn(OXZ) 2 which is the host material, to form an emitting layer 4 .
  • a positive voltage and a negative voltage were respectively applied to the hole injection electrode 2 and the electron injection electrode 6 in each of the organic electroluminescent devices in the example 1 and the comparative examples 1 and 2, to find the highest luminance obtained in the organic electroluminescent device and the applied voltage at that time, and each of the organic electroluminescent devices was caused to emit light having luminance of 100 cd/m 2 , to find a time period elapsed until the luminance is reduced by half.
  • the results were shown in the following Table 1.
  • the organic electroluminescent devices in the examples 2 to 7 and the comparative examples 3 and 4 were obtained in the same manner that in the example 1 except that an emitting layer 4 was formed using only the above-mentioned host material in the comparative example 3, while 2′,3′-naphtha-2,3-fluorenone indicated by the following chemical formula 7, 2,3-anthrafluorene indicated by the following chemical formula 8, 2,3-benzofluorenone indicated by the following chemical formula 9, picene indicated by the following chemical formula 10, ovalene indicated by the following chemical formula 11, pyrene quinone indicated by the following chemical formula 12, and dioxazine carbazole indicated by the following chemical formula 13 were doped at a ratio of 2 % by weight as a dopant into the above-mentioned host material, respectively, in the example 2, the example 3, the example 4, the example 5, the example 6, the example 7, and the comparative example 4.
  • a positive voltage and a negative voltage were respectively applied to the hole injection electrode 2 and the electron injection electrode 6 in each of the organic electroluminescent devices in the examples 2 to 7 and the comparative examples 3 and 4, to find the highest luminance obtained in the organic electroluminescent device and the applied voltage at that time, and each of the organic electroluminescent devices was caused to emit light having luminance of 100 cd/m 2 , to find a time period elapsed until the luminance is reduced by half.
  • the results were shown in the following Table 2.
  • the organic electroluminescent devices in the examples 8 to 19 and the comparative examples 5 and 6 were obtained in the same manner that in the example 1 except that an emitting layer 4 was formed using only the above-mentioned host material in the comparative example 5, while 1′,2′-naphtha-2,3,-fluorene indicated by the following chemical formula 15, 2′,1′-naphtha-1,2-fluorene indicated by the following chemical formula 16, 1,12-benzperylene indicated by the following chemical formula 17, 4,5-benzpyrene indicated by the following chemical formula 18, benzo(a)pyrene indicated by the following chemical 19, naphthapyrene indicated by the following chemical formula 20.
  • 1,3-bis(1-pyrenyl)propane indicated by the following chemical formula 21 5,6,11,12-tetramethyl naphthacene indicated by the following formula 22, 9,10-bis(phenylethynyl)anthracene indicated by the following chemical formula 23, fluoracene indicated by the following chemical formula 24, fluorocyclene indicated by the following chemical formula 25, perylene indicated by the following chemical formula 26, 1,2,3,4-tetraphenyl-1,3-cyclopentadiene indicated by the following chemical formula 27 were doped at a ratio of 2% by weight as a dopant into the above-mentioned host material, respectively, in the example 8, the example 9, the example 10, the example 11, the example 12, the example 13, the example 14, the example 15, the example 16, the example 17, the example 18, the example 19, and the comparative example 6.
  • a positive voltage and a negative voltage were respectively applied to the hole injection electrode 2 and the electron injection electrode 6 in each of the organic electroluminescent devices in the examples 8 to 19 and the comparative examples 5 and 6, to find the highest luminance obtained in the organic electroluminescent device and the applied voltage at that time, and each of the organic electroluminescent devices was caused to emit light having luminance of 100 cd/m 2 , to find a time period elapsed until the luminance is reduced by half.
  • the results were shown in the following Table 3.
  • organic electroluminescent devices in examples 20 to 31 and comparative examples 7 and 8 only the emitting layer 4 in the organic electroluminescent device in the above-mentioned example 1 was changed, and tris(8-quinolinol)aluminum (hereinafter referred to as Alq 3 ) indicated by the following chemical formula 28 was used as a host material.
  • Alq 3 tris(8-quinolinol)aluminum
  • the organic electroluminescent devices in the examples 20 to 31 and the comparative examples 7 and 8 were obtained in the same manner that in the example 1 except that an emitting layer 4 was formed using only the above-mentioned host material in the comparative example 7, while 1′,2′-naphtha-2,3-fluorenone indicated by the following chemical formula 29, 2′,1′-naphtha-1,2-fluorenone indicated by the following chemical formula 30, rubicene indicated by the following chemical formula 31, 1,2-benzpentacene indicated by the following chemical formula 32, 5,6,11,12-tetraphenyl naphthacene (rubrene) indicated by the following chemical formula 33, rubrene peroxide indicated by the following chemical formula 34, naphthacene quinone indicated by the following chemical formula 35, pentacene-5,12-quinone indicated by the following chemical formula 36, pentacene-6,13-quinone indicated by the following chemical formula 37, 3,9-perylene quinone indicated by the following
  • a positive voltage and a negative voltage were respectively applied to the hole injection electrode 2 and the electron injection electrode 6 in each of the respective organic electroluminescent devices in the examples 20 to 31 and the comparative examples 7 and 8, to find the highest luminance obtained in the organic electroluminescent device and the applied voltage at that time, and each of the organic electroluminescent devices was caused to emit light having luminance of 100 cd/m 2 , to find a time period elapsed until the luminance is reduced by half.
  • the results were shown in the following Table 4.
  • a transparent hole injection electrode 2 having a thickness of 2000 ⁇ was formed using the above-mentioned ITO on a glass substrate 1 , and an emitting layer 4 having a thickness of 500 ⁇ obtained by doping 2% by weight of 2′,3′-naphtha-2,3-fluorene indicated by the following chemical formula 42 as a dopant into a host material composed of polyvinyl carbazole (PVCz) indicated by the following chemical formula 41, a first electron transport layer 5 a, which has hole blocking properties, having a thickness of 200 ⁇ using a triazole derivative (TAZ) indicated by the following chemical formula 43, a second electron transport layer 5 b having a thickness of 300 ⁇ using Alq 3 indicated by the foregoing chemical formula 28, and an electron injection electrode 6 having a thickness of 2000 ⁇ using a magnesium-indium alloy were laminated on the injection electrode 2 , as shown in FIG. 5 .
  • PVCz polyvinyl carbazole
  • TEZ triazole derivative
  • Organic electroluminescent devices in examples 33 to 35 and comparative examples 9 and 10 were obtained in the same manner as that in the above-mentioned example 32 except that only the emitting layer 4 in the organic electroluminescent device in the above-mentioned example 33 was changed, to form an emitting layer 4 using only the above-mentioned PVCz which is a host material in the comparative example 9, while the dopant to be doped into the host material using the above-mentioned PVCz was changed in the examples 33 to 35 and the comparative example 10, that is, 2% by weight of 2,3-benzofluorene indicated by the following chemical formula 44, 1,2-benzofluorene indicated by the following chemical formula 45, dibenzo(a,h)anthracene indicated by the following chemical formula 46, and 1,4-bis(5-phenyl-2-oxazolyl)benzene (hereinafter referred to as POPOP) indicated by the following chemical formula 47 were respectively doped in the example 33, the example 34, the example 35,
  • a positive voltage and a negative voltage were respectively applied to the hole injection electrode 2 and the electron injection electrode 6 in each of the organic electroluminescent devices in the examples 32 to 35 and the comparative examples 9 and 10, to find the highest luminance obtained in the organic electroluminescent device and the applied voltage at that time, and each of the organic electroluminescent devices was caused to emit light having luminance of 100 cd/m 2 , to find a time period elapsed until the luminance is reduced by half.
  • the results were shown in the following Table 5.
  • the organic electroluminescent device in the present invention is not limited to those in the above-mentioned examples, and can be embodied by being suitably changed in a range in which the gist thereof is not changed.
  • the organic electroluminescent device in the present invention in forming an emitting layer having a dopant doped into a host material, a dopant having a condensed ring obtained by condensing three or more rings is used, the difference in the HOMO between the host material and the dopant is in a range from ⁇ 0.3 eV to +0.3 eV, the film stability of the emitting layer is improved, and an organic material in the emitting layer is prevented from being crystallized due to heat or the like at the time of light emission, so that stable and uniform light emission can be performed for a long time, and excitation energy is efficiently moved from the host material to the dopant. Therefore, luminous efficiency in the organic electroluminescent device is improved, so that high luminance is obtained.
  • the present invention can be further optimized by using as these materials materials having a substituent group, for example, —C 6 H 5 , —CH 3 , —C 2 H 5 , —C(CH 3 ) 3 , —OCH 3 , —OCOCH 3 , —OH, —NH 2 , —N(CH 3 ) 2 , —N(C 6 H 5 ) 2 , —NC 12 H 8 , —NHCOCH 3 , —NH 3 , —CF 3 , —NO 2 , —CN, —COCH 3 , and —CO 2 C 2 H 5 .
  • a substituent group for example, —C 6 H 5 , —CH 3 , —C 2 H 5 , —C(CH 3 ) 3 , —OCH 3 , —OCOCH 3 , —OH, —NH 2 , —N(CH 3 ) 2 , —N(C 6 H 5 ) 2 ,

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US20030089904A1 (en) * 2001-10-15 2003-05-15 Fujitsu Limited Electrically conducting organic compound and electronic device
KR100389195B1 (ko) * 2000-12-08 2003-06-27 (주)신화엔지니어링종합건축사사무소 청색광을 고효율로 발산하는 유기 전계 발광체
US6613454B2 (en) * 2000-04-21 2003-09-02 Tdk Corporation Organic EL device
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